In November 1999, in Miami, Florida, Donald Trump gave a speech to the Cuban American National Foundation. It was the first day of the billionaire’s first bid for the White House: he was seeking to be the Reform Party’s candidate for the following November’s presidential election.

“As you know—and the people in this room know better than anyone—putting money and investing money in Cuba right now doesn’t go to the people of Cuba,” Trump said to the crowd of Cuban-Americans, a key voting bloc in an important swing state. “It goes to Fidel Castro,” a “bad guy in every respect,” he said. Trouble is, just months earlier, Trump’s hotel and casino company, in a breach of U.S. law, spent money traveling to the communist island.

A new investigative report by Newsweek shows that in 1998, Trump Hotels & Casino Resorts, using a consulting firm as a front, spent more than $68,000 on a trip to Cuba. The country at the time was completely shut-off by the U.S.: American companies could not do business there, with the exception of charitable organizations.

Representatives from the consulting firm Seven Arrows Investment and Development Corp. went to Cuba on behalf of Trump’s company, according to a former executive. Their goal on the island was to lay down groundwork in case the U.S.’s trade embargo with Cuba–in place since 1962–was lifted. Seven Arrows reps traveled throughout the island, meeting with government officials, bankers, and business leaders. Following the trip, Seven Arrows said it traveled to the island on behalf of a Catholic charity.

Months after the Cuba trip, Seven Arrows submitted a bill to Trump Hotels & Casino Resorts for the expenses incurred on its trip. At the time, American companies were banned from doing any business with Cuba. In order for a charitable organization to conduct work on the island, it had to obtain a license from the Office of Foreign Assets Control, or OFAC.

Failing to do so would amount to a breach of federal law, trade law experts told Newsweek. There are no records that show Trump Hotels & Casino Resorts, or Seven Arrows, obtained the necessary permits.

The former executive with Trump’s company, who spoke to Newsweek anonymously, said Trump knew about the Cuba trip. He also said that prior to the trip to Cuba, European companies contacted Trump Hotel & Casino Resorts about investing in Cuba.

In 1998, Trump’s company was in dire financial straits. According to its financial filings with the Securities and Exchange Commission, Trump Hotels & Casino Resorts lost $39.7 million that year, while its stock price plunged.

The details of Trump’s potentially illegal foray into Cuba in 1998 might prove damning for his current presidential bid–though it could also be buried beneath his other business-related scandals–but he will not face a legal windfall nearly two decades later. For one, the statue of limitations for bringing a suit has run its course. And OFAC is understaffed, legal analysts told Newsweek, so a costly and time-consuming investigation into Trump’s Cuba adventure is highly unlikely.

Trump’s campaign is denying the allegations brought forth by the Newsweek report. In an interview on ABC Thursday morning, Kellyanne Conway, Trump’s campaign manager, said he paid money, but “decided not to invest there,”

Alec Siegel

Alec Siegel is a staff writer at Law Street Media. When he’s not working at Law Street he’s either cooking a mediocre tofu dish or enjoying a run in the woods. His passions include: gooey chocolate chips, black coffee, mountains, the Animal Kingdom in general, and John Lennon. Baklava is his achilles heel. Contact Alec at ASiegel@LawStreetMedia.com.

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